Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst
Seven mono- and dihydroxycholesterols were prepared by direct C–H oxidation of the cholestane skeleton with a recently developed Ru(Bpga) catalyst (Ru(Bpga) = [RuCl (bpga) (PPh<sub>3</sub>)] Cl; bpga = 2-(bis(pyridin-2-ylmethyl)amino)-<i>N</i>-(2,6-dimethylphenyl)acetamide))....
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-12-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/1/225 |
| _version_ | 1827668147220512768 |
|---|---|
| author | Yui Fujii Makoto Yoritate Kana Makino Kazunobu Igawa Daiki Takeda Daiki Doiuchi Katsuhiko Tomooka Tatsuya Uchida Go Hirai |
| author_facet | Yui Fujii Makoto Yoritate Kana Makino Kazunobu Igawa Daiki Takeda Daiki Doiuchi Katsuhiko Tomooka Tatsuya Uchida Go Hirai |
| author_sort | Yui Fujii |
| collection | DOAJ |
| description | Seven mono- and dihydroxycholesterols were prepared by direct C–H oxidation of the cholestane skeleton with a recently developed Ru(Bpga) catalyst (Ru(Bpga) = [RuCl (bpga) (PPh<sub>3</sub>)] Cl; bpga = 2-(bis(pyridin-2-ylmethyl)amino)-<i>N</i>-(2,6-dimethylphenyl)acetamide)). Due to the high selectivity of the Ru(Bpga) complex for tertiary C–H, the reaction afforded a mixture of 25-, 20-, 17-, and 14-oxygenated cholesterols that could be easily separated by high-performance liquid chromatography. These results suggest that late-stage C–H oxidation could be a viable strategy for preparing candidate metabolites of biologically important molecules. |
| first_indexed | 2024-03-10T03:30:05Z |
| format | Article |
| id | doaj.art-9be7554e0d6f4dcfa53aa1b90458ccdb |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:30:05Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-9be7554e0d6f4dcfa53aa1b90458ccdb2023-11-23T11:58:31ZengMDPI AGMolecules1420-30492021-12-0127122510.3390/molecules27010225Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) CatalystYui Fujii0Makoto Yoritate1Kana Makino2Kazunobu Igawa3Daiki Takeda4Daiki Doiuchi5Katsuhiko Tomooka6Tatsuya Uchida7Go Hirai8Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Fukuoka, JapanGraduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Fukuoka, JapanGraduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Fukuoka, JapanInstitute for Materials Chemistry and Engineering, Integrated Research Consortium on Chemical Sciences (IRCCS), Kyushu University, Kasuga 816-8580, Fukuoka, JapanGraduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Fukuoka, JapanDepartment of Chemistry, Graduate School of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Fukuoka, JapanInstitute for Materials Chemistry and Engineering, Integrated Research Consortium on Chemical Sciences (IRCCS), Kyushu University, Kasuga 816-8580, Fukuoka, JapanDepartment of Chemistry, Graduate School of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395, Fukuoka, JapanGraduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Fukuoka, JapanSeven mono- and dihydroxycholesterols were prepared by direct C–H oxidation of the cholestane skeleton with a recently developed Ru(Bpga) catalyst (Ru(Bpga) = [RuCl (bpga) (PPh<sub>3</sub>)] Cl; bpga = 2-(bis(pyridin-2-ylmethyl)amino)-<i>N</i>-(2,6-dimethylphenyl)acetamide)). Due to the high selectivity of the Ru(Bpga) complex for tertiary C–H, the reaction afforded a mixture of 25-, 20-, 17-, and 14-oxygenated cholesterols that could be easily separated by high-performance liquid chromatography. These results suggest that late-stage C–H oxidation could be a viable strategy for preparing candidate metabolites of biologically important molecules.https://www.mdpi.com/1420-3049/27/1/225cholesteroloxysterolC–H oxidationRu (bpga)25-hydroxycholesteroldihydroxycholesterol |
| spellingShingle | Yui Fujii Makoto Yoritate Kana Makino Kazunobu Igawa Daiki Takeda Daiki Doiuchi Katsuhiko Tomooka Tatsuya Uchida Go Hirai Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst Molecules cholesterol oxysterol C–H oxidation Ru (bpga) 25-hydroxycholesterol dihydroxycholesterol |
| title | Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst |
| title_full | Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst |
| title_fullStr | Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst |
| title_full_unstemmed | Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst |
| title_short | Preparation of Oxysterols by C–H Oxidation of Dibromocholestane with Ru(Bpga) Catalyst |
| title_sort | preparation of oxysterols by c h oxidation of dibromocholestane with ru bpga catalyst |
| topic | cholesterol oxysterol C–H oxidation Ru (bpga) 25-hydroxycholesterol dihydroxycholesterol |
| url | https://www.mdpi.com/1420-3049/27/1/225 |
| work_keys_str_mv | AT yuifujii preparationofoxysterolsbychoxidationofdibromocholestanewithrubpgacatalyst AT makotoyoritate preparationofoxysterolsbychoxidationofdibromocholestanewithrubpgacatalyst AT kanamakino preparationofoxysterolsbychoxidationofdibromocholestanewithrubpgacatalyst AT kazunobuigawa preparationofoxysterolsbychoxidationofdibromocholestanewithrubpgacatalyst AT daikitakeda preparationofoxysterolsbychoxidationofdibromocholestanewithrubpgacatalyst AT daikidoiuchi preparationofoxysterolsbychoxidationofdibromocholestanewithrubpgacatalyst AT katsuhikotomooka preparationofoxysterolsbychoxidationofdibromocholestanewithrubpgacatalyst AT tatsuyauchida preparationofoxysterolsbychoxidationofdibromocholestanewithrubpgacatalyst AT gohirai preparationofoxysterolsbychoxidationofdibromocholestanewithrubpgacatalyst |